Incorporating Morpholine and Oxetane into Benzimidazolequinone Antitumor Agents: The Discovery of 1,4,6,9-Tetramethoxyphenazine from Hydrogen Peroxide and Hydroiodic Acid-Mediated Oxidative Cyclizations

被引：10

作者：

Conboy, Darren ^{[1
]}

Mirallai, Styliana, I ^{[2
]}

Craig, Austin ^{[2
]}

McArdle, Patrick ^{[2
]}

Al-Kinani, Ali A. ^{[1
]}

Barton, Stephen ^{[1
]}

Aldabbagh, Fawaz ^{[1
,2
]}

机构：

[1] Kingston Univ, Sch Life Sci Pharm & Chem, Dept Pharm, Penrhyn Rd, Kingston Upon Thames KT1 2EE, Surrey, England

[2] Natl Univ Ireland Galway, Sch Chem, Univ Rd, Galway H91 TK33, Ireland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 15期

关键词：

RING-FUSED BENZIMIDAZOLES; OXIDOREDUCTASE; NQO1; QUINONES; BIOSYNTHESIS; HETEROCYCLES; ETHERS; WATER;

D O I：

10.1021/acs.joc.9b01427

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactivity of hydrogen peroxide and catalytic hydroiodic acid toward 3,6-dimethoxy-2-(cycloamino)anilines is tunable to give ring-fused benzimidazoles or 1,4,6,9-tetramethoxyphenazine in high yield. Mechanisms via a detected nitroso-intermediate are proposed for oxidative cyclization and the unexpected intermolecular displacement of the oxazine. An aqueous solution of molecular iodine is capable of the same transformations. Oxidative demethylation gave targeted benzimidazolequinones, including without cleavage of the incorporated oxetane.

引用

页码：9811 / 9818

页数：8